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US5340802A
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Peptide analog type-B CCK receptor ligands
Assignee: Abbott Laboratories
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Filing: 1993-01-29
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Granted: 1994-08-23
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Expires: 2013-01-29
Abstract
Abstract Peptide analog type-B CCK receptor ligands or pharmaceutically-acceptable salts thereof, which are useful for treating central nervous system disorders, substance abuse, gastrointestinal disorders, endocrine disorders, eating-related disorders and for the treatment of shock, respiratory and cardiocirculatory insufficiencies.
Inventors
- 👤 Kazumi Shiosaki
- 👤 Alex M. Nadzan
- 👤 David S. Garvey
- 👤 Youe-Kong Shue
- 👤 Mark S. Brodie
- 👤 Mark W. Holladay
- 👤 John Y.-L. Chung
- 👤 Michael D. Tufano
- 👤 Paul D. May
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 10:47
CPC Classifications
C; C07; C07K; C07K5/00; C07K5/04; C07K5/10; C07K5/1002; C07K5/1016; C07K5/02; C07K5/0207; C07K5/08; C07K5/0802; C07K5/0804; C07K5/0808; C07K5/1024; A; A61; A61K; A61K38/00
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
495 words
A compound of the formula: A--B--Y--Z (I) or a pharmaceutically-acceptable salt thereof, wherein A is either ##STR27## wherein R 1 is selected from the group consisting of (i) hydrogen, (ii) halogen, (iii) hydroxy, (iv) C 1 -C 6 -alkoxy, (v) thio-C 1 -C 6 -alkoxy, (vi) amino, (vii) (N-protected)amino, (viii) C 1 -C 6 -alkylamino, (ix) (N-protected)-C 1 -C 6 -alkylamino, and (x) R 5 --R 4 --C(O)--N(R 3 )--, wherein R 3 is hydrogen or C 1 -C 6 -alkyl; R 4 is C 1 -C 6 -alkylene or C 2 -C 6 -alkenylene; and R 5 is phenyl or substituted phenyl; R 2 is naphthyl, mono-substituted naphthyl, phenyl, mono-substituted phenyl, benzohet, or mono-substituted benzohet; or ##STR28## wherein R 6 is selected from the group consisting of (i) hydrogen, (ii) hydroxy, (iii) halogen, (iv) C 1 -C 6 -alkyl, (v) amino, (vi) C 1 -C 6 -alkylamino, and (vii) di-C 1 -C 6 -alkylamino; and R 7 is hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -alkanoyl; B is either ##STR29## wherein R 3 is as defined above; and R 8 is C 1 -C 6 -alkyl or mono-substituted C 1 -C 4 -alkylene, wherein the substituent is C 1 -C 6 -alkoxy or thio-C 1 -C 6 -alkoxy; or ##STR30## wherein R 9 is C 2 -C 4 -alkylene; R 10 is absent or is oxygen or sulfur; and R 11 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, thio-C 1 -C 6 -alkoxy, or mono-substituted C 1 -C 4 -alkylene, wherein the substituent is C 1 -C 6 -alkoxy or thio-C 1 -C 6 -alkoxy; Y is ##STR31## wherein R 12 is carboxy or tetrazolyl; and Z is ##STR32## wherein R 3 is as defined above; R 13 is selected from the group consisting of (i) C 1 -C 6 -alkyl, (ii) cyclo-C 3 -C 8 -alkyl, (iii) Het, (iv) mono-substituted Het, (v) naphthyl, (vi) mono-substituted naphthyl, (vii) phenyl, (viii) mono-substituted phenyl, (ix) benzohet, and (x) mono-substituted benzohet; and R 14 is --NHR 15 , wherein R 15 is hydrogen, hydroxy, methyl or amino; ##STR33## wherein R 14 is as defined above; R 16 is selected from the group consisting of (i) hydrogen, (ii) C 1 -C 6 -alkyl, (iii) halogen, (iv) halo-C 1 -C 6 -alkyl, (v) C 1 -C 6 -alkoxy, (vi) thio-C 1 -C 6 -alkoxy, (vii) hydroxy, (viii) C 1 -C 6 -alkoxycarbonyl, (ix) carboxy, (x) amino, (xi) C 1 -C 6 -alkylamino, (xii) di-C 1 -C 6 -alkylamino, (xiii) nitro, and (xiv) --OSO 3 H; or ##STR34## wherein R 13 and R 14 are as defined above; with the proviso that when A is selected from either option (a) for A above where R 1 is amino, (N-protected)amino or R 5 --R 4 --C(O)--N(R 3 )--, then B must be selected from option (b) for B above or Z must be selected from options (2) or (3) for Z above.
Claim 2
Dependent Claim
495 words
A compound of the formula: A--B--Y--Z (I) or a pharmaceutically-acceptable salt thereof, wherein A is either ##STR27## wherein R 1 is selected from the group consisting of (i) hydrogen, (ii) halogen, (iii) hydroxy, (iv) C 1 -C 6 -alkoxy, (v) thio-C 1 -C 6 -alkoxy, (vi) amino, (vii) (N-protected)amino, (viii) C 1 -C 6 -alkylamino, (ix) (N-protected)-C 1 -C 6 -alkylamino, and (x) R 5 --R 4 --C(O)--N(R 3 )--, wherein R 3 is hydrogen or C 1 -C 6 -alkyl; R 4 is C 1 -C 6 -alkylene or C 2 -C 6 -alkenylene; and R 5 is phenyl or substituted phenyl; R 2 is naphthyl, mono-substituted naphthyl, phenyl, mono-substituted phenyl, benzohet, or mono-substituted benzohet; or ##STR28## wherein R 6 is selected from the group consisting of (i) hydrogen, (ii) hydroxy, (iii) halogen, (iv) C 1 -C 6 -alkyl, (v) amino, (vi) C 1 -C 6 -alkylamino, and (vii) di-C 1 -C 6 -alkylamino; and R 7 is hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -alkanoyl; B is either ##STR29## wherein R 3 is as defined above; and R 8 is C 1 -C 6 -alkyl or mono-substituted C 1 -C 4 -alkylene, wherein the substituent is C 1 -C 6 -alkoxy or thio-C 1 -C 6 -alkoxy; or ##STR30## wherein R 9 is C 2 -C 4 -alkylene; R 10 is absent or is oxygen or sulfur; and R 11 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, thio-C 1 -C 6 -alkoxy, or mono-substituted C 1 -C 4 -alkylene, wherein the substituent is C 1 -C 6 -alkoxy or thio-C 1 -C 6 -alkoxy; Y is ##STR31## wherein R 12 is carboxy or tetrazolyl; and Z is ##STR32## wherein R 3 is as defined above; R 13 is selected from the group consisting of (i) C 1 -C 6 -alkyl, (ii) cyclo-C 3 -C 8 -alkyl, (iii) Het, (iv) mono-substituted Het, (v) naphthyl, (vi) mono-substituted naphthyl, (vii) phenyl, (viii) mono-substituted phenyl, (ix) benzohet, and (x) mono-substituted benzohet; and R 14 is --NHR 15 , wherein R 15 is hydrogen, hydroxy, methyl or amino; ##STR33## wherein R 14 is as defined above; R 16 is selected from the group consisting of (i) hydrogen, (ii) C 1 -C 6 -alkyl, (iii) halogen, (iv) halo-C 1 -C 6 -alkyl, (v) C 1 -C 6 -alkoxy, (vi) thio-C 1 -C 6 -alkoxy, (vii) hydroxy, (viii) C 1 -C 6 -alkoxycarbonyl, (ix) carboxy, (x) amino, (xi) C 1 -C 6 -alkylamino, (xii) di-C 1 -C 6 -alkylamino, (xiii) nitro, and (xiv) --OSO 3 H; or ##STR34## wherein R 13 and R 14 are as defined above; with the proviso that when A is selected from either option (a) for A above where R 1 is amino, (N-protected)amino or R 5 --R 4 --C(O)--N(R 3 )--, then B must be selected from option (b) for B above or Z must be selected from options (2) or (3) for Z above.
Claim 3
Dependent Claim
23 words
A compound of claim 1, wherein B is selected from option (b) for B, or A is selected from option (b) for A.
Claim 4
Dependent Claim
48 words
A compound of claim 1, wherein A is selected from option (a), with R 1 being amino or (N-protected)amino and option (b) with R 6 being hydrogen, and B is selected from option (b) with R 10 being absent, and R 11 being C 1 -C 6 -alkyl.
Claim 5
Dependent Claim
62 words
A compound according to claim 1 which is selected from the group consisting of: Ctp-Leu-Asp-Phe-NH 2 ; BOC-Trp-Leu-Asp-Tiq-NH 2 ; Ctp-Leu-Asp-(NMe)Phe-NH 2 ; Ctp-Leu-Asp-(dehydro)Phe-NH 2 ; BOC-Trp-Tpp-Asp-Phe-NH 2 ; Ctp-Tpp-Asp-Phe-NH 2 ; Ctp-Tpp-Asp-(NMe)Phe-NH 2 ; Ctp-Cpp-Asp-Phe-NH 2 ; BOC-Trp-Tpp-Asp-Trp-NH 2 ; Ctp-Tpp-Asp-α-Nal-NH 2 ; Ctp-Tpp-Asp-β-Nal-NH 2 ; Ctp-Tpp-Asp-Cha-NH 2 ; Ctp-(1,4-thiazane-3-carbonyl)-Asp-Phe-NH 2 ; and Ctp-Pip-Asp-Phe-NH 2 , or a pharmaceutically-acceptable salt thereof.
Claim 6
Dependent Claim
3 words
Ctp-Tpp-Asp-Phe-NH 2 .
Claim 7
Dependent Claim
3 words
Ctp-Tpp-Asp-Phe-NH 2 .
Claim 8
Dependent Claim
23 words
A pharmaceutical composition for treating CCK type-B receptor-related disorders comprising a pharmaceutically-acceptable carrier and a therapeutically-effective amount of a compound of claim 1.
Claim 9
Dependent Claim
34 words
A method for mimicking the effects of CCK on CCK type-B receptor comprising administering to a human or other mammal in need of such treatment a therapeutically-effective amount of a compound of claim 1.
Claim 10
Dependent Claim
32 words
A method for treating schizophrenia, convulsions, neurodegeneration and Parkinson's disease comprising administering to a human or other mammal in need of such treatment a therapeutically-effective amount of a compound of claim 1.
Claim 11
Dependent Claim
30 words
A method for treating gastrointestinal and endocrine disorders comprising administering to a human or other mammal in need of such treatment a therapeutically-effective amount of a compound of claim 1.
Claim 12
Dependent Claim
28 words
A method for treating hemorrhagic shock comprising administering to a human or other mammal in need of such treatment a therapeutically-effective amount of a compound of claim 1.
Claim 13
Dependent Claim
28 words
A method for treating alcohol addiction comprising administering to a human or other mammal in need of such treatment a therapeutically-effective amount of a compound of claim 1.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1997-08-22 | 1998-02-21 | 1998-08-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2001-08-22 | 2002-02-21 | 2002-08-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2005-08-22 | 2006-02-21 | 2006-08-23 | $7700.00 | Window Closed / Lapsed |